Gymnastatin A - Compound Card

Gymnastatin A

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Gymnastatin A

Structure
Zoomed Structure
  • Family: Fungi - Gymnoascaceae
  • Kingdom: Fungi
  • Class: Amide
    • Subclass: Acyl Amide
Canonical Smiles CCCCCCC(/C=C(/C=C/C(=O)NC1CC2(OC1O)C=C(Cl)C(=O)C(=C2)Cl)\C)C
InChI InChI=1S/C23H31Cl2NO4/c1-4-5-6-7-8-15(2)11-16(3)9-10-20(27)26-19-14-23(30-22(19)29)12-17(24)21(28)18(25)13-23/h9-13,15,19,22,29H,4-8,14H2,1-3H3,(H,26,27)/b10-9+,16-11+
InChIKey NGXMXBNROHVABT-AKYRVGECSA-N
Formula C23H31Cl2NO4
HBA 4
HBD 2
MW 456.41
Rotatable Bonds 9
TPSA 75.63
LogP 4.89
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.57
Exact Mass 455.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Gymnascella dankaliensis Gymnoascaceae Fungi 166389

Showing of synonyms

  • Hammerschmidt L, Aly AH, et al. (2015). Cytotoxic acyl amides from the soil fungus Gymnascella dankaliensis. Bioorganic and Medicinal Chemistry,2015,23,712-719. [View] [PubMed]
Pubchem: 102427406

No compound-protein relationship available.

Structure

SMILES: O1CCCC12C=CC(=O)C=C2

Level: 0

Mol. Weight: 456.41 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.86
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.4

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.6
Plasma Protein Binding
47.53
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
1.23
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.65
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.12
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.13
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-9.31
Rat (Acute)
2.81
Rat (Chronic Oral)
2.1
Fathead Minnow
5.07
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
446.67
Hydration Free Energy
-5.71
Log(D) at pH=7.4
4.55
Log(P)
5.29
Log S
-4.67
Log(Vapor Pressure)
-8.49
Melting Point
103.22
pKa Acid
8.09
pKa Basic
5.23
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.9622
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.9622
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.9376
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.9376
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9064
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9064
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9042
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9042
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9039
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9039
Ascorbate-specific PTS system EIIC component P39301 ULAA_ECOLI Escherichia coli 3 0.8929
Ascorbate-specific PTS system EIIC component P39301 ULAA_ECOLI Escherichia coli 3 0.8929
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8790
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8790
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8745
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8745
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8541
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8541
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.8380
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.8380
Bacteriorhodopsin P02945 BACR_HALSA Halobacterium salinarum 3 0.8267
Bacteriorhodopsin P02945 BACR_HALSA Halobacterium salinarum 3 0.8267
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8091
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8091
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8058
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8058
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8043
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8043
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.8038
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.8038
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8031
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8031
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7973
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7973
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7964
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7964
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7952
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7952
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7940
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7940
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7915
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7915
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7906
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7906
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7872
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7872
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7847
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7847
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7847
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7847
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7838
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7838
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7813
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7813
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7803
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7803
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7797
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7797
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7778
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7778
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7776
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7776
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7751
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7751
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7747
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7747
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7738
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7738
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7723
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7723
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7715
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7715
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7706
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7706
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7679
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7679
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7649
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7649
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7646
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7646
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7637
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7637
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7632
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7632
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7627
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7627
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7600
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7600
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7583
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7583
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7560
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7560
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 3 0.7486
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 3 0.7486
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7484
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7484
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7479
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7479
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7474
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7474
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7457
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7457
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7442
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7442
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7417
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7417
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7417
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7417
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7400
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7400
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7371
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7371
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7365
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7365
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7350
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7350
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 3 0.7346
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 3 0.7346
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7343
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7343
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7341
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7341
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7339
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7339
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7337
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7337
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7318
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7318
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7314
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7314
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7312
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7312
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7310
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7310
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7302
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7302
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7296
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7296
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7279
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7279
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.7275
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.7275
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7273
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7273
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7264
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7264
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7261
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7261
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7251
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7251
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7249
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7249
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7247
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7247
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7244
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7244
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7222
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7222
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7164
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7164
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7155
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7155
Tachylectin-2 Q27084 TAL2_TACTR Tachypleus tridentatus 3 0.7131
Tachylectin-2 Q27084 TAL2_TACTR Tachypleus tridentatus 3 0.7131
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7119
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7119
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7112
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7112
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7054
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7054
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7033
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7033
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7024
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7024

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